"On to the Next One" and why Jay-Z loves shouting out Andy Warhol, Jean-Michel Basquiat, and Damien Hirst.

Hova Goes MoMA

The video for Jay-Z's "On to the Next One," which he released on New Year's Eve, is the sort of densely packed curio cabinet that encourages repeat visits. In the lyrics, Jay-Z promises that no matter where you are, he's one step ahead of you—"on that next shit"—and the video is his attempt to illustrate that boast in unexpected ways. For starters: No other rap video has featured flaming basketballs, power cords whipping madly beneath fluorescent bulbs, and a fidgety evil clown. Photographed in the sumptuous black and white of a Richard Avedon portrait, these images and others combine to form a seductive, faintly menacing cipher. The gleaming 2011 Jaguar XJ that appears in several shots isn't the only thing tantalizingly beyond our grasp—so is the meaning behind most of what we see. We're left to scratch our heads as to what, for instance, that ram skull is about, or why the woman crouched on that stack of crates is holding martial-arts fighting sticks. Jay-Z, the implication goes, totally knows.

With the "On to the Next One" clip, Jay-Z and the director Sam Brown jumble bluntly evocative status symbols—a bulging stack of hundreds, Armand de Brignac champagne—with more mysterious symbolism—a bell jar containing taxidermy birds, a swirling ink blot, those whipping cords (which, it bears mentioning, are lifted from the 2002 video for Interpol's "Obstacle 1"). Some of the most memorable shots in the video are of black paint pouring down a diamond-covered skull. The skull is a replica of "For the Love of God," a Damien Hirst sculpture that the British artist fabricated for about $30 million in 2007 and sold for a purported $100 million (to a group of investors that includes the Ukrainian billionaire Viktor Pinchuk and, oddly, Hirst himself). Like the Jaguar XJ, Hirst's skull telegraphs extreme wealth, but that's not all: Screaming its value while begging to be mulled over, it's a status symbol and a puzzle in one.

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This is not the first time Jay-Z has made an art-world reference in his work. For several years, he's mentioned Andy Warhol and Jean-Michel Basquiat in his rhymes, discussed Hirst in his interviews, and put pieces by Hirst and Takashi Murakami on conspicuous display in his videos and stage sets. Nor is he the only hip-hop star to do so: Kanye West and Pharrell Williams have collaborated with Murakami on videos and sculptures, and West has blogged enthusiastically about Jeff Koons and Urs Fischer, among other artists; Swizz Beatz, who produced "On to the Next One" and who appears in the video wearing a jacket painted with a Keith Haring design, has rapped about collecting Basquiats, and he Twitters regularly about such Chelsea-centric matters as hanging out with Larry Gagosian.

In the late '90s, so many rappers rapped about Cadillac Escalades that the SUVs are still synonymous with hip-hop—albeit in a crusty, parodic way. At first glance, these nods to art stars may seem something like Escalades 2.0: A fresh way for Jay-Z and his cohort to not just broadcast their wealth but also their class, their conversance with high society, distancing themselves from those hopeless cases stuck on last-year's-model obsessions, who have never even heard of Miami Basel (where Jay-Z and his wife Beyoncé went shopping last year).

This explanation is partially true, but if all Jay-Z wanted to do was keep us abreast of his ever-swelling fortune and ascent into rarefied social circles, he might rap about, say, the wildly expensive canvases of Julian Schnabel—iconic wall candy of the hyper-riche—or any number of MoMA blue-chippers. (It's not hard to think of rhymes for Brice Marden or Lucien Freud.) Why is it Hirst, Murakami, and Basquiat who pop up in his videos and his verses?

Maybe it's because he sees them as kindred spirits. Like Jay-Z, who once calculated his personal fortune during the course of a song, Murakami and Hirst make art that is largely about the markets they exist in and the wealth they generate. Murakami designed monograms for Louis Vuitton, which in turn installed a functioning boutique in his 2008 MOCA retrospective. Hirst's "For the Love of God" is largely about its own value, both before and after its art-world debut; the question of how much it cost to buy the stones, and how much of a markup Hirst's imprimatur can sustain, is part of the narrative of the piece. This feels especially relevant to Jay-Z—when he raps, during the excellent Blueprint 3 outtake "Ain't I," that he paid $250,000 for the beat, he similarly writes the song's exorbitant cost into the song itself.

Jay-Z's commonalities with Hirst go further. Like Jay, who signed a "360-degree deal" with LiveNation, leaving his longtime record label so that he might benefit more fully from the tremendous revenue he generates, Hirst recently bypassed the gallery system and sold $200 million worth of his art directly at auction, via Sotheby's. And, as in Jay-Z's music, Hirst's meditations on wealth frequently accompany meditations on mortality. The Hirst pieces Jay-Z gravitates toward are those in which this theme is especially prominent: the diamond skull, which references memento mori, and which Hirst has described as a laugh "in the face of" death; the spin-art skull paintings that dominate Jay-Z's "Blue Magic" video, works that, produced in a batch of 300 by a team of assistants, nod both to the "death of the author" and supply-and-demand economics.

Jay-Z seems to feel a kinship of a different sort with Jean-Michel Basquiat. An insight into his appreciation comes in one of the best, most dexterous rhymes of his career, a 2006 freestyle over Kanye West's "Grammy Family" instrumental. Jay-Z begins by rapping that he's "inspired by Basquiat," and puts the artist—born in Brooklyn to Puerto Rican and Haitian parents in 1960, an international star by his early 20s, dead of a drug overdose at 27—in a continuum of fallen icons that includes Malcolm X, Michael Jackson, and Kurt Cobain. In this company, Basquiat figures both as a civil rights hero—a type to whom Jay-Z often compares himself—and a cautionary tale. Whereas Hirst's art mingles wealth and death, Basquiat's career (which begins at about the same time as hip-hop itself) mingles fame and death. With Basquiat's demise in mind, Jay-Z, the invincible hustler who refuses to lose, grapples with the idea of the self-destructive success story: "Game stays the same, the name changes/ So it's best for those not to overdose on being famous."

The pair's artistic preoccupations overlap, too. Like Jay-Z, who has toyed in several of his songs with popular conceptions of himself as violent, misogynist, or otherwise brutish, Basquiat also played in his scratchy canvases with the notion of the black "primitive"—a term that came under scrutiny in the '80s art world, and which had been applied to Basquiat early on. "Every step you take they remind you, you ghetto," Jay-Z raps on the "Grammy Family" freestyle.

It's perhaps curious that Jean-Michel Basquiat is the only black art star to really penetrate the hip-hop airspace, at least as explicit references go, even as the field of black art stars has grown more crowded. (Kanye West did once link on his blog to a roundup of "promising young black artists.") For Jay-Z, at least, his interest in the artists he champions seems to have as much if not more to do with their relationship to money as with their relationship to race. (Of course, he regularly describes the African-American amassment of wealth as a political act in itself.) On 2009's "Already Home," he brags, "I'm a work of art, I'm a Warhol already," and, indeed, Jay-Z has realized Andy Warhol's vision of the artist-as-corporate-entity more completely than Warhol, with his Factory and roster of superstars, ever did.

Jay-Z has this in common with Murakami and Hirst, and the clue to the affinities between all three artists—Brooklyn rapper, Japanese kawaiienthusiast, and U.K. cow-slicer—may be that they made some of their most famous work riding the crests of giant tidal waves of money. In the early '00s, thanks respectively to a broadening global market for rap and the hedge-fund-era rise of the superrich collector, both the hip-hop and art worlds were more flush with cash than ever before, and Jay-Z, Murakami, and Hirst were among the biggest beneficiaries, poster boys—and narrators—of the boom times. "I'm not a businessman, I'm a business, man," Jay-Z famously rapped. It could make a nice title for the next Hirst exhibit.

Jonah Weiner is a contributing editor at Rolling Stone and a contributing writer at the New York Times Magazine.